Journal article
Syntheses in enantiopure form of four diastereoisomeric naphthopyranquinones derived from aphid insect pigments
Organic & Biomolecular Chemistry, Vol.3(2)
2005
Abstract
The first syntheses are described of the four enantiopure naphthopyranquinones (1R,3R,4S)- and (1R,3R,4R)-3,4-dihydro-4,7,9-trihydroxy-1, 3-dimethylnaphtho[2,3-c]pyranquinone (quinone A 1 and quinone A' 2) and their two C-3 epimers, the (1R,3S,4S)- and (1R,3S,4R)-diastereoisomers 5 and 6, using enantiopure lactate as the source of asymmetry. Key factors in these syntheses are the maintenance of stereochemical integrity throughout the sequences and intramolecular diastereoselective cyclisations of the titanium phenolates of phenolic lactaldehydes. For these cyclisations the differing degree of diastereoselectivity is explained as are the stereochemistries of the product 2-benzopyran-4,5-diols.
Details
- Title
- Syntheses in enantiopure form of four diastereoisomeric naphthopyranquinones derived from aphid insect pigments
- Authors/Creators
- R. Aggarwal (Author/Creator) - Murdoch UniversityR.G.F. Giles (Author/Creator) - Murdoch UniversityI.R. Green (Author/Creator) - University of the Western CapeF.J. Oosthuizen (Author/Creator) - Murdoch UniversityC.P. Taylor (Author/Creator) - Murdoch University
- Publication Details
- Organic & Biomolecular Chemistry, Vol.3(2)
- Publisher
- Royal Society of Chemistry
- Identifiers
- 991005543238007891
- Murdoch Affiliation
- School of Chemical and Mathematical Science
- Language
- English
- Resource Type
- Journal article
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- Collaboration types
- Domestic collaboration
- International collaboration
- Citation topics
- 1 Clinical & Life Sciences
- 1.219 Cancer Drugs
- 1.219.1527 Naphthoquinone Derivatives
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry